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{{chembox |
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{{chembox |
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| verifiedrevid = 414427308 |
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| verifiedrevid = 443691169 |
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| ImageFile = Dimethylamine-2D.png |
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| ImageSize = 160px |
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| ImageFile = Me2NH.svg |
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| ImageClass = skin-invert-image |
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| ImageAlt = Structural formula |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile1 = Dimethylamine-3D-balls-B.png |
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| ImageSize1 = 180px |
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| ImageSize = 200 |
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| ImageName = Skeletal formula of dimethylamine |
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| ImageAlt1 = Ball-and-stick model |
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| IUPACName=Dimethylamine |
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| ImageFile1 = Dimethylamine-3D-balls.png |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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| Section1={{Chembox Identifiers |
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| PubChem = 674 |
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| ImageSize1 = 100 |
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| ImageName1 = Ball and stick model of dimethylamine |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PIN = ''N''-Methylmethanamine |
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| OtherNames = (Dimethyl)amine |
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|Section1={{Chembox Identifiers |
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| CASNo = 124-40-3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 674 |
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| ChemSpiderID = 654 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII = ARQ8157E0Q |
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| UNII = ARQ8157E0Q |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 204-697-4 |
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| UNNumber = 1032 |
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| KEGG = C00543 |
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| KEGG = C00543 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| InChI = 1/C2H7N/c1-3-2/h3H,1-2H3 |
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| MeSHName = dimethylamine |
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| InChIKey = ROSDSFDQCJNGOL-UHFFFAOYAM |
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| ChEBI = 17170 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 120433 |
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| ChEMBL = 120433 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| RTECS = IP8750000 |
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| Beilstein = 605257 |
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| Gmelin = 849 |
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| 3DMet = B00125 |
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| SMILES = CNC |
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| StdInChI = 1S/C2H7N/c1-3-2/h3H,1-2H3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C2H7N/c1-3-2/h3H,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ROSDSFDQCJNGOL-UHFFFAOYSA-N |
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| StdInChIKey = ROSDSFDQCJNGOL-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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| CASNo=124-40-3 |
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|Section2={{Chembox Properties |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Properties_ref = <ref>{{cite web|title=Dimethylamine|url=http://webbook.nist.gov/cgi/cbook.cgi?ID=C124403&Mask=1#Thermo-Gas|work=NIST Chemistry WebBook|publisher=National Institute of Standards and Technology|access-date=15 February 2022|location=USA}}</ref><ref>{{Cite web|title=Dimethylamine 38931 - ≥99.0%|url=https://www.sigmaaldrich.com/US/en/product/aldrich/38931 |
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| ChemSpiderID = 654 |
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|work=Aldrich|publisher=Sigma-Aldrich Co.|access-date=15 February 2022}}</ref> |
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| ChEBI = 17170 |
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| SMILES = N(C)C |
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| C=2 | H=7 | N=1 |
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| Formula = (CH<sub>3</sub>)<sub>2</sub>NH |
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| Appearance = Colorless gas |
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| Odor = Fishy, ammoniacal |
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| Density = 649.6 kg m<sup>−3</sup> (at 25 °C) |
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| MeltingPtK = 180.15 |
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| BoilingPtK = 280 to 282 |
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| Solubility = 1.540 kg L<sup>−1</sup> |
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| LogP = −0.362 |
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| VaporPressure = 170.3 kPa (at 20 °C) |
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| HenryConstant = 310 μmol Pa<sup>−1</sup> kg<sup>−1</sup> |
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| pKb = 3.29 |
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|Section3={{Chembox Thermochemistry |
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| DeltaHf = −21 to −17 kJ mol<sup>−1</sup> |
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}} |
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|Section4={{Chembox Hazards |
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| GHSPictograms = {{gHS flame}} {{gHS corrosion}} {{gHS exclamation mark}} |
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| GHSSignalWord = '''DANGER''' |
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| HPhrases = {{h-phrases|220|302|315|318|332|335}} |
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| PPhrases = {{p-phrases|210|261|280|305+351+338}} |
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| NFPA-H = 2 |
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| NFPA-F = 4 |
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| NFPA-R = 0 |
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| FlashPtC = −6 |
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| FlashPt_notes = (liquid) |
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| AutoignitionPtC = 401 |
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| ExploLimits = 2.8–14.4% |
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| PEL = TWA 10 ppm (18 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0219}}</ref> |
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| IDLH = 500 ppm<ref name=PGCH/> |
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| REL = TWA 10 ppm (18 mg/m<sup>3</sup>)<ref name=PGCH/> |
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| LC50 = 4700 ppm (rat, 4 hr)<br/>4540 ppm (rat, 6 hr)<br/>7650 ppm (mouse, 2 hr)<ref name=IDLH>{{IDLH|124403|Dimethylamine}}</ref> |
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| LD50 = 698 mg/kg (rat, oral)<br/>316 mg/kg (mouse, oral)<br/>240 mg/kg (rabbit, oral)<br/>240 mg/kg (guinea pig, oral)<ref name=IDLH/> |
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}} |
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|Section5={{Chembox Related |
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| OtherFunction_label = amines |
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| OtherFunction = {{unbulleted list|]|]|]|]|]|]}} |
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| OtherCompounds = {{unbulleted list|]}} |
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}} |
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| Section2={{Chembox Properties |
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| Formula=C<sub>2</sub>H<sub>7</sub>N |
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| MolarMass=45.08 g/mol |
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| Density=0.67 g/cm<sup>3</sup> (21 °C, 1 atm) |
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| Solubility=354 g/100 mL |
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| Appearance=Colorless gas with pungent odor |
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| Solvent=Water |
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| MeltingPtC=-92.2 |
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| BoilingPtC=7 |
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| pKa=10.64<ref>Hall, H.K., ''J. Am. Chem. Soc.'', '''1957''', ''79'', 5441.</ref> |
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| Dipole= |
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| Section3={{Chembox Thermochemistry |
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| DeltaHf= -18.422 kJ/mol |
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| Entropy= |
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| Section4={{Chembox Hazards |
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| EUClass=Highly flammable ('''F+''')<br/>Harmful ('''Xn''') |
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| EUIndex=612-001-00-9 |
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| NFPA-H=3 |
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| NFPA-F=4 |
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| NFPA-R=0 |
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| RPhrases={{R12}} {{R20}} {{R37/38}} {{R41}} |
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| SPhrases={{S2}} {{S16}} {{S26}} {{S39}} |
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| FlashPt=Flammable gas |
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| Autoignition=400 °C |
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| ExploLimits=2.8–14.4% |
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| RTECS=IP8750000 |
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}} |
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| Section5={{Chembox Supplement |
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}} |
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| Section6={{Chembox Related |
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| OtherFunctn=]<br/>]<br/>] |
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| Function=amine |
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}} |
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'''Dimethylamine''' is an ] with the formula (CH<sub>3</sub>)<sub>2</sub>NH. This ] is a colorless, flammable liquified gas with an ]-like odor. Dimethylamine is generally encountered as a solution in water at concentrations up to around 40%. In 2005, an estimated 270,000 tons were produced.<ref name=Ullmann>A. B. van Gysel, W. Musin "Methylamines" in Ullmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH Verlag, Weinheim. {{DOI|10.1002/14356007.a16 535}}</ref> |
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'''Dimethylamine''' is an ] with the formula (CH<sub>3</sub>)<sub>2</sub>NH. This ] is a colorless, flammable gas with an ]-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.<ref name=Ullmann>{{Ullmann |doi=10.1002/14356007.a16_535|title=Methylamines|year=2000|last1=Van Gysel|first1=August B.|last2=Musin|first2=Willy}}</ref> |
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==Structure and properties== |
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==Structure and synthesis== |
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The molecule consists of a ] ] with two ] ]s and one ]. Dimethylamine is a ] and the ] of the ] CH<sub>3</sub>-NH<sub>2</sub><sup>+</sup>-CH<sub>3</sub> is 10.73, a value above ] (10.64) and ] (9.79). |
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The molecule consists of a ] ] with two ] ]s and one ]. Dimethylamine is a ] and the ] of the ] CH<sub>3</sub>-{{chem|NH|2|+}}-CH<sub>3</sub> is 10.73, a value above ] (10.64) and ] (9.79). |
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Dimethylamine reacts with acids to form salts, such as dimethylamine hydrochloride, an odorless white solid with a melting point of 171.5 °C. Dimethylamine is produced by ] reaction of ] and ] at elevated temperatures and high pressure:<ref>{{cite journal |
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Dimethylamine reacts with acids to form salts, such as dimethylamine hydrochloride, an odorless white solid with a melting point of 171.5 °C. Dimethylamine is produced by ] reaction of ] and ] at elevated temperatures and high pressure:<ref>{{cite journal |
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| author = Corbin D.R.; Schwarz S.; Sonnichsen G.C. |
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| author = Corbin D.R. |
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| author2 = Schwarz S. |
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| author3 = Sonnichsen G.C. |
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| title = Methylamines synthesis: A review |
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| title = Methylamines synthesis: A review |
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| journal = Catalysis Today |
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| journal = Catalysis Today |
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| doi = 10.1016/S0920-5861(97)00003-5 }} |
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| doi = 10.1016/S0920-5861(97)00003-5 }} |
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</ref> |
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</ref> |
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:{{Chem2|2 CH3OH + NH3 → (CH3)2NH + 2 H2O}} |
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:2 CH<sub>3</sub>OH + NH<sub>3</sub> → (CH<sub>3</sub>)<sub>2</sub>NH + 2 H<sub>2</sub>O |
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==Natural occurrence== |
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Dimethylamine is found quite widely distributed in animals and plants, and is present in many foods at the level of a few mg/kg.<ref>{{cite journal | last1 = Neurath | first1 = G. B. | display-authors = etal | year = 1977 | title = Primary and secondary amines in the human environment | journal = Food and Cosmetics Toxicology | volume = 15 | issue = 4| pages = 275–282 | doi=10.1016/s0015-6264(77)80197-1| pmid = 590888 }}</ref> |
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==Uses== |
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==Uses== |
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Dimethylamine is a precursor to several industrially significant compounds.<ref name=Ullmann/><ref>Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, pages 3284-3286</ref> It reacts with ] to give dimethyl], a precursor to a family of chemicals widely used in the ] of ]. The solvents ] and ] are derived from dimethylamine. It is raw material for the production of many ]s and ]s, such as dimefox and ], respectively. The ] ] is derived from dimethylamine. The ] ] is found in ]s and cleaning compounds. ], a rocket fuel, is prepared from dimethylamine. |
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Dimethylamine is a precursor to several industrially significant compounds.<ref name=Ullmann/><ref>''Ashford's Dictionary of Industrial Chemicals'', 3rd edition, 2011, pages 3284-3286</ref> It reacts with ] to give dimethyl ], a precursor to ] and other chemicals used in the ] of ]. ] is manufactured by reacting dimethylamine and ].<ref>Frank, H., 2007. Preparation of N, N-Dimethylaminoethoxyethanol by Reacting Reacting Di-methylamine with Ethylene Oxide US Patent</ref> Other methods are also available producing streams rich in the substance which then need to be further purified.<ref>US8907084B2 - Process for the preparation of 2-(2-aminoethoxy) ethanol (2AEE) and morpholine with 2AEE: morpholine >3 - Google Patents</ref> The solvents ] and ] are derived from dimethylamine. It is raw material for the production of many ]s and ]s, such as ] and ], respectively. The ] ] is derived from dimethylamine. The ] ] is found in ]s and cleaning compounds. ], a rocket fuel, is prepared from dimethylamine.<ref name=Schirmann>{{Ullmann|doi=10.1002/14356007.a13_177|title= Hydrazine|year= 2001 |last1=Schirmann |first1=Jean-Pierre |last2=Bourdauducq|first2= Paul|isbn= 3-527-30673-0}}</ref> |
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:(CH<sub>3</sub>)<sub>2</sub>NH + NH<sub>2</sub>Cl → (CH<sub>3</sub>)<sub>2</sub>NNH<sub>2</sub> ⋅ HCl |
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It is an attractant for ]s.<ref name="Merck">''The Merck Index, 10th Ed.'' (1983), p.470, Rahway: Merck & Co.</ref> |
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== Biochemistry == |
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==Reactions== |
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It is basic, in both the ]<ref>{{Cite book |last1=Laurence |first1=Christian |title=Lewis basicity and affinity scales: data and measurement |last2=Le Gall |first2=Jean-François |date=2010 |publisher=Wiley-Blackwell |isbn=978-0-470-74957-9 |location=Oxford |pages=50–51}}</ref><ref>{{cite journal |author1=Cramer, R. E. |author2=Bopp, T. T. |year=1977 |title=Graphical display of the enthalpies of adduct formation for Lewis acids and bases |journal=Journal of Chemical Education |volume=54 |pages=612–613 |doi=10.1021/ed054p612}} The plots shown in this paper used older parameters. Improved E&C parameters are listed in ]. </ref> and ] senses. It easily forms '''dimethylammonium''' salts upon treatment with acids. Deprotonation of dimethylamine can be effected with ]s. The resulting LiNMe<sub>2</sub>, which adopts a cluster-like structure, serves as a source of Me<sub>2</sub>N<sup>−</sup>. This lithium amide has been used to prepare volatile metal complexes such as ] and ]. |
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The ] utilizes dimethylamine as a ] for communication.<ref>{{cite journal |author=Zhang AQ, Mitchell SC, Smith RL |title=Dimethylamine formation in the rat from various related amine precursors |journal=] |volume=36 |issue=11 |pages=923–7 |year=1998 |month=November |pmid=9771553 |doi= 10.1016/S0278-6915(98)00074-X|url=}}</ref> |
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It reacts with many carbonyl compounds. Aldehydes give aminals. For example reaction of dimethylamine and ] gives ]:<ref>{{cite journal |doi=10.15227/orgsyn.059.0153|title=Regioselective Mannich Condensation with Dimethyl(Methylene)ammonium Trifluoroacetate: 1-(Dimethylamino)-4-methyl-3-pentanone |
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DMA undergoes ] under weak acid conditions to give ]. This animal ] has been detected and quantified in human urine samples and it may also arise from nitrosation of DMA by nitrogen oxides present in acid rain in highly industrialized countries. |
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|first1=Michel|last1=Gaudry|first2=Yves|last2=Jasor|first3=Trung Bui |last3=Khac|journal=Org. Synth.|year=1979|volume=59|page=153}}</ref> |
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: 2 (CH<sub>3</sub>)<sub>2</sub>NH + CH<sub>2</sub>O → <sub>2</sub>CH<sub>2</sub> + H<sub>2</sub>O |
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It converts esters to dimethylamides. |
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==Safety== |
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Dimethylamine is not very toxic with the following LD<sub>50</sub> values: 736 mg/kg (mouse, i.p.); 316 mg/kg (mouse, p.o.); 698 mg/kg (rat, p.o.); 3900 mg/kg (rat, dermal); 240 mg/kg (guinea pig or rabbit, p.o.).<ref>Chemical Information Profile for Dimethylamine Borane, National Toxicology Program, NIEHS, NIH (2008), p.4: http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/DimethylamineBorane508.pdf</ref> |
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Although not acutely toxic, dimethylamine undergoes ] to give ], a carcinogen. |
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==See also== |
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==See also== |
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*] |
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*] (1,3-dimethypentylamine) |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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== External links == |
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==External links== |
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* {{ICSC|0260|02}} (gas) |
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* {{ICSC|0260|02}} (gas) |
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* {{ICSC|1485|14}} (aqueous solution) |
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* {{ICSC|1485|14}} (aqueous solution) |
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* {{PGCH|0219}} |
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* {{PGCH|0219}} |
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* from ] |
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